Ask any stylish person, and they’ll tell you an oversized shirt is a wardrobe staple. Even with a long history of women wearing men’s shirts, the classic look gets a contemporary update each season, thanks to new styling tips and tricks.
As with any ‘oversized’ item, you’re guaranteed a bit of leeway in finding the right size and fit. The greatest perk of this clothing item is that you don’t need to worry too much about fine tailoring or even picking your usual size.
However, one mustn’t assume there are no traps when picking an oversized shirt. You may need different lengths, fits and colours, depending on how you want to wear it. Often worn untucked and flowing, an oversized shirt is an eternal favourite because it can be thrown-on over any outfit.
Yet, some might find themselves in a love-hate relationship with the occasionally shapeless look of a big, cotton button-up. In such a case, the secret to styling your oversized shirt is in tucking, tying, layering and accessorising.
To find out how, one only need to look at the thousands of ways the look has been styled, spanning over 100 years in the fashion zeitgeist.
If you’re wondering where the oversized shirt trend began, you could pinpoint it to the first and second world wars, when women started wearing more utilitarian clothing—like trousers and button-ups—to complete traditionally ‘male’ jobs left vacant on the home front. This was propelled into style cannon by Coco Chanel, who loved to borrowed from menswear to create her groundbreaking designs.
In Old Hollywood, gender-bending style icons, like Katharine Hepburn and Marlene Dietrich, elevated the oversized shirt to celebrity status. Fast forward to the 1970s and you have Diane Keaton rocking suits and ties over a classic, white men’s shirt on the red carpet.
Over the years, the oversized has become synonymous with ‘effortlessly chic’ style—the kind of go-to item in one’s capsule wardrobe that you reach for whenever you want to look fresh and cool. Often worn untucked and flowing, an oversized shirt is an eternal favourite because it can be thrown-on over almost any outfit.
It’s the kind of item you can wear 101 ways. However, if you’re wondering how it should look in 2025 and beyond, here’s what we can tell you about how to style your oversized shirt.
Oversized Shirt + Jeans
A classic look, an oversized shirt and jeans can be dressed up or down whether you’re headed to the office or just running errands. Perhaps the secret to styling it is in the shoe. For the office, you may want to wear your shirt and jeans with a pair of kitten heels, sleek ballet flats or loafers. For a more relaxed look, you’re better going for sandals or sneakers. Somewhere in between? Wear your fave boots.
Darcy Shirt Blue Stripe
ELKA COLLECTIVE
Florence Small Shoulder Bag
OROTON
Harper mid-rise wide-leg jeans
AGOLDE
Saint sunglasses
CHIMI
Oversized Shirt + Mini Skirt
This expert combo mixes the best of feminine and masculine styles for a tailored and youthful look, no matter your age. You can wear your oversized shirt untucked to create the almost-illusion of you wearing no pants at all, or tuck it in for a more polished, French style. Wear with loafers or sneakers for a preppy, ivy league look, or elongate your legs with strappy sandals or heels.
Deacon Unisex Shirt
VIKTORIA & WOODS
Suede Skirt
WITCHERY
Riviere cord & leather sandals
MIU MIU
Slim Rectangular Signet Ring
MEJURI
Oversized Shirt + Sheer Skirt
All over fashion week you can see It Girls pairing their oversized shirts with the latest elegant skirts, particularly the recently-popular sheer maxi skirts. If wearing a slim, column-style skirt, feel free to let your shirt billow to create contrast between your top and bottom. Pair with your choice of shoes. (The Copenhagen style set would surely encourage an ‘ugly shoe’.)
Lark Shirt
CAMILLA AND MARC
Claudia Ballet Flats
DOF STUDIOS
Saint Midi Skirt
WITH JEAN
Nim x Pared Style 01
PARED EYEWEAR
Oversized Shirt + Shorts
Jorts and Bermuda shorts are suddenly hanging up in everyone’s wardrobes, but how can you make it work with a collared shirt? Firstly, let the tails of the shirt flow to avoid looking like a sit-com dad. If you’re off to work, throw on a blazer and kitten heels. Grabbing a matcha and hitting the markets? Wear your oversized shirt with thongs and a bandana for the ultimate cool-girl style.
Oversized shirt
& OTHER STORIES
Adler Pleated Wool Twill Shorts
LOULOU DE SAISON
Nora Hand Knit Headscarf
CASA CLARA
Small Saddle Bag with Strap
DIOR
Oversized Shirt + Blazer
The Annie Hall-look has made a comeback in recent years, thanks to the androgynous womenswear styling at Saint Laurent. You can lean into the slouchy style by pairing with low-waisted trousers, flat shoes and an oversized bag, or channel your inner ‘man in finance’ by buttoning up to the top and adding a tie.
Voile Shirt
TOTEME
Vermont Blazer
VIKTORIA & WOODS
Bateman Trouser
VIKTORIA & WOODS
Lene Satin Tie
THE FRANKIE SHOP
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